Mistake I Would Make Again
by kitten195
Summary: Jill is the baby of the Wincheseter clan. Her dad and big brothers think she's still the little kid that they all know and love. What will happen when she gets pregnant? How will her family react. Will she even tell them? Oh, the drama.
1. Chapter 1

The Mistake I Would Make Again ( Dean 21, Sam 17, Jillian newly 15)

"This can't be happening,' Jill pleaded in the small, dirty reststop bathroom. 'Come on, it was only one night, damn it.' she cursed in pure desperation. She kept her eyes on the mirror to prevent her from looking at the home pregnancy test she deliberately placd face-down from unconsciously glancing at it and knowing what her future would hold before she was mentally prepared for any outcome. On the other hand, she never thought she would be undoubtedly ready. Also, if she was to remain in the bathroom until she was, her dad and older brothers would kick the door down, causing an unneccessary scene.

'NO Jill, you ARE stronger than this. Just be a grown woman and look at the stick,' she encouraged. 'Oh, what am I talking about? I'm not a woman, i'm just a norma... well a teenage girl anyway. I shouldn't have to deal with this,' her counter ego shot back.

" Oh screw it,' she thought. 'I'm looking at the damn test,' and with no further room for discussion so she couldn't chicken out, because she had terribly hard time buying the damn thing under her family's nose in the first place.

She abrupty picked up the test and took one last look at herself in the mirror, knowing full-well that her life a some-what normal teen could be over with if there were two pink lines on the other side of the stick. She flipped the little white test over.

Two pink lines, two pink lines, two pink lines, was all her mind could register. She dropped the test in the sink with a clatter, backing up until her back touched the cold plastered wall. Without caring that the floor was most likey carrying The Plague, she slowly slid down it, letting out the breathe she had been holding for a fair amount of time.

She was pregnant. She couldn't seem to wrap her head around it. I mean, how could she? The life that she had before was officially over. Never to be heard from again.

A sudden banging on the door brought her out of her current state. She wanted whoever was on the other side of the door to just go away. She needed to be alone so she could cry or even scream at the top of her lungs, whichever one came first.  
"Jill, hurry up, ok. Dad wants to be on the road like, right now so we can get to Bobby's by morning," came her brother's shout through the rotting door.

It was Sam. Jill seemed to calm down a little when she heard her big brothers voice. There were certain things that always calmed her down. One was Dean's arms wrapping her in one of his normal bear hugs he would always save for her and her alone. The other was Sam's voice. The same one that sang to her when she was a little girl when she started getting worried when their daddy didn't come home for days on end. Two things that may have seemed so very simple to any other person, were her world. Her lifeline. The two things that never failed to be there and comfort her no matter what the crisis was or how far apart they were.

Finding her voice and willing it to be steady was not an easy task, but when she thought she accomplished it, she sent out her reply.

"Sure Sam, just give me a minute ok," she said standing up and one again standing in front of the mirror trying to regain her composure so nobody would realize something was off.

"Sure, just hurry up. You really don't wanna get dad in a bad mood because you were doddling though. Remember, we'll be in the car with him for most likely the next eight long know how stressful that could be."

And with that, all she was left with, was silence.

'She would tell them when the time was right,' she told herself as she took a few dep calming breaths. 'The time just wasn't now,' and without even daring to look at the pregnancy test, she turned on her heel towards the door. She turned the knob and opened the door, letting a ray a bright sunshine light up the dark restroom. She stepped out and with aquick survey, picked her family out of the crowd and put on a normal, nothing-was-wrong face and rejoined her group with the weight of the world on her shoulders. 


	2. Chapter 2

One more week turned into two and then drifted in to three. Jill knew she couldn't keep it a secret much longer, due to her constantly growing stomache. She tried to cover up her lack of appetite and vomiting in the morning as best she could, but the weight issue was not going to get any better for the time being. She tried her best to cover it up with loose shirts and sweat pants, which could work for a little bit due to the Summer dying off and Winter was taking hold, but somebody was bound to notice her not wearing her regular jeans and boots. Winter was her favorite season, and she always enjoyed it. Not this time around.

Any normal year, she would wait in anticipation for the Winter months. She loved everything about Winter. The time you get just to stare out of the window at the cold world, while your inside snuggled up next to a heater. How you fall asleep to the faint pitter-patter of rain on the roof. Her favorite part was the first snowfall. She always knew when it would happen, and no matter what time it was, without fail, she would go get her two older brothers and drag them outside with her. They would gripe and grumble about it, but she knew they enjoyed it just as much as she did. It wasn't gonna happen this year. There would be anger and secrets between the three Winchester sibilings. She couldn't help but wonder, where would she be this time next year, would it be like it was or would she have a little baby to introduce to the snow. That she didn't know and she hated not knowing something.

Sam had been giving her these quizzical looks lately but she tried her hardest to ignore them. She hoped that he didn't know what was going on with her. She was going to tell him, when the time was right.

So there she sat on the windowsill of their current "home." Her dad and Dean were off researching their next hunt. There had been another fight earlier about hunting that, as usual, revolved around Dad and Sam. She usual tried her best to ignore them. She hated when Sam stated another fight with Dad. It always ended badly. And without fail, somehow Dean and I were brought into it. It ended with Sam screaming something about Dean being a perfect little soldier and the bad hunting incident that led to me almost dying. That had led to Dad and Dean leaving for the library. I immediately turned on my hell and walked back into my room with out giving Sam a second glance. Usually she would try and make him feel better, you know, watch movies, eat tons of junk food or just take a walk with him. She loves Sam to death but the constant arguing has got to stop. She can't take this much more of this.

She plops down on her bed, turning the radio softly on to her favorite dial to drown out the eerie stillness of the house. Just as she was starting to finally relax, the sound of her door quietly opening had her giving a slight sigh, ten sat up to Sam leaning against the doorframe. His arms are crossed and he gives her his 'I know your dirty little secret' look. Before she could ask him what he's doing, he blurts out,

"Your pregnant, aren't you," he said in a voice a little above a whisper.

Her heart started pounding so hard that her chest started hurting. She scrambled to make up a lie, 'Tell him no, you stupid girl,' her mind screamed. As much as her mind told her to say something, the words refused to make it to her mouth. Then she heard herself talking.

" Yes," she barely whispered. She almost thought he didn't hear her until his big brown eyes completely melted into understanding and compassion. He walked over to the bed and sat down right next to her. He wrapped his long arms around her and held her close to his chest. She let him. He whispered that she one thing that she desperately needed to hear.

"It's gonna be ok honey, I promise. I'm gonna help you get through this," he soothed.

And just like that, her barriers broke away and she justed bawled. She let the sobs wrack her body as she held on to Sam's jacket. And for the first time in a long time, she finally saw the light at the end of a dark tunnel. 


	3. Chapter 3

Letting her tears finally out about how scared she is was exactly what she needed. Jill was so relieved that she wasn't the only one carrying the secret around on her shoulders any longer. She could finally talk to somebody about all her worries and fears.

She was glad the person was Sam. He was the one family member that understood and comforted rather than get angry and yell. Just by the way that he held her, she had this feeling that everything was going to be alright for the first time since she found out she was pregnant.

After what seemed like hours, she quieted her sobs and gently lifted her head off Sam's chest to look into his big brown eyes. 'Here comes the talk,' she thought. 'Might as well get it over with.'

" Sam, I'm sorry I let you down," she whispered and looked away from the look of pity written on his face.

He simply reached out his hand and cupped her chin in his hands and guided her face to get her eyes to meet his. Once he was satisfied that he had her full attention, he spoke.

"Jill honey, You didn't let me down," he sighed. "You just made a mistake like everyone on Earth has; and like everyone on Earth, you have to live with the consequences of your actions. Let me just tell you this, you are not alone in this. I will stand by your side no matter what happens. You have my word on that," he promised.

She looked at him in complete and utter relief. He still cared about her. For that she was so grateful. Then another thought came into her head that had her hopes sinking. Dad and Dean.

"Thank you Sam, now how are we gonna tell Dean," she put out while biting her lower lip.

Sam was just about to answer when a voice came from the doorway. Their older brothers voice.

"Tell me what," he inquired leaning on the door frame.

Both Sam and Jill jumped a foot in the air before snapping their necks toward the sound of Dean. They were each quietly hoping that Dean only heard the last bit of the conversation, now was not the time for a big blowout.

Sam felt Jill completly tense up next to him on the bed. He seemed to find himself the power to form words and the courage to speak them.

"Dean, what are you doing back so early," he started, trying to change the subject.

He just gave look that meant he knew what Sam was doing.

"I decided to come home early and spend some time with my little sibilings. Now, why don't you tell me what you don't know how to tell me," he said, rounding his way back to the main subject.

"It's nothing really Dean, lets just drop it," Jill put in nervously.

Dean knew something big was up with Sam and Jill , and was not just gonna let it go without a fight.

"Sorry sis, I'm now officially intriqued. Now spill," he stated, coming in to the room. Taking a seat on her second-hand dresser and folding his arms across his chest. His sibilings haven't been this sneaky since the time they found a stray dog wandering the alleyway and had insisted on keeping it.

After giving Sam one of his quick, you-better-tell-me-now-because-I-will-find-out looks. And then turned his attention to Jill. Once he actually got a good loook at her face, he could see the mascara tear tracks running down her cheecks. All hopes if him leaving it along were eliminated.

Sam was starting to get agitated. Dean would not leave them alone and He wanted some time to talk to Jill alone before anyone else found out, Dean included. He could sense that Jill's breathing was eratic and she was figiting on the bed next to him. He reached over and gave her hand a comforting squeeze. 'She's gonna need it,' he thought. Sam mentally decided that he would be the one to tell him. Jill didn't need that right now.

"Ok, Dean. Before I tell you, you need to promise not to over-react," Sam cautiously began. He had to tell him just the right way. Otherwise he would hit the roof, so to speak, and would most likely end up with an all out screaming match between the two brothers.

Dean agreed with a nod of the head and took a deep breathe. He didn't know what they were gonna say, so he was trying to prepare himself for anything.

Sam opened his mouth when he heard his sister speak.  
"Dean, I'm pregnant," Jill jumped in before she even knew that she had spoken.

Dean's attention completely turned to the outburst of his litle sister. 'What did she just say!?!' he thought. 


	4. Chapter 4

"What did you just say," he siad as calmly and quietly as he could. He didn't want to flip out if he just misheard her. He was hoping that he just heard her wrong.

Jill took a deep breath before repeating what she just said.

"I said, I'm pregnant," she said while trying to keep her eratic heartbeat from beating against her chest.

Dean was speechless was one word for it. He would open his mouth to say something, then shut it again. He repeated the motion for about three more times, before the initial shock wore off.

"YOU"RE WHAT??' he screamed at the top of his lungs. Both Sam and Jill jumped in their seats.

"I CAN"T BELIEVE YOU'RE STUPID ENOUGH TO GET YOURSELF PREGNANT,'" he screeched through gritted teeth.

Sam noticed that Dean's face was now the color of a tomato. If this was any other circumstance, he would have pointed that out, but now does not seem like the right time. He just hoped that the neighbors wouldn't hear and think that somebodys being murdered over here, and think it was their civic obligation to call 911.

But now that he thinks about it, and the color of his big brother's head, he just might want to call the police himself before he either kills Jill, or has a heart attack himself.

(About five minutes later)

Dean seemed at loss of words now. For the last five minutes he screamed, he screamed at his sister which that has never happened before, to the point where he almost forget she was there and continued his rant while pacing the room and hitting unsuspecting furniture. He was soo mad. He couldn't even think right.

Sam looked over at Jill to see her eyes completely filled with tears. He didn't know what to do. That was until Jill let out a sob and covered her mouth with one hand and let the tears stream down her cheecks, leaving fresh rivers down her face.

Sam scooted over until he was right next to her, and took her in his arms. He let her cry once again on him.

The crying broke Dean out of his anger-filled trance. He turned to look at the bed and what he found broke his heart. Sam was holding a crying Jill in his arms.

He didn't know what to do, so he did the only thing that he could do. He left. He left the room in record time, got in his car, and drove away from the house where he left his broken-hearted sister in Sam's care. 


	5. Chapter 5

Sam was holding Jill in his arms for the second time in one night. If it wasn't for the adrenaline rushing through him, he would barely be functional. The only two things keeping him going were his sister and waiting til Dean came home so he could clock him one.

'He didn't need to act like that. We're gonna have enough problems when dad finds out,' he bitterly thought, before he queitly sighed at the thought of their dad and his own reaction. 'Great, another worry, and another blowout,' he thought.

After about another ten minutes, Jill seemed to competely tire out and sag into Sam's already tear-soaked shirt. The last thought she had before she fell into a troublesome sleep was 'What was she going to do, Dean hates her.'

Once Sam was positive she was asleep, he gently eased her back into the bed and covered her with a nearby purple and orange blanket. As he bent down to kiss her forehead, he wiped away a few stray tears,and quietly left the room.

Once the bedroom door was closed, he let his head fall against the wood, as he closed his eyes. 'What a night,' he thought, as he pushed himself upright. He slowly made his way into the kitchen, making sure to check every one of the salt lines that would keep them safe tonight.

He was just opening the fridge in search of something to eat, when he heard the familiar sound of the Impala's engine pull into the driveway. All thought of eating suddenly vanished as his rage retook control. The 'John Winchester temper,' as many might call it. he shut the refridgerator door and made his way up the front steps just as Dean was slowly making his way up the walk. His head was down and he was feebly kicking a pebble out of his way.

Sam crossed his arms and stood his ground, right in front of the door. He wasn't going to let him in the house if he was going to start anything else with Jill tonight. She just got to sleep, and the last thing she needed was her Jackass-big brother waking her up, because he wants to yell some more.

When Dean make it to the front steps, he raised his gaze to look directly in Sam's eye. They stayed that way for awhile, until Dean broke the silence.

"Sam, I'm sorry for the way I a," Dean began. That was until Sam cut him off with a blow to the jaw. Dean stumbled back afew steps before he reagined his balance. His hand went up to comfort his face.

Sam was in shock. He really hit his brother. His protector. The man that would do anything for him. He was down-right terrified! Dean was going to kill him.

He did his best not to look scared. Instead he clenched his jaw, and made sure his head was being held high.

Dean recovered quickly and would have struck back if it was anybody else. 'Hell, he probably did deserve it,' he thought.

One look at Sam and he could tell he was scared of what his reaction would be. He was trying to hide it, but Dean always had the ability to see right through his little brother, and sister.

"Man, he messed up with that one,' he thought.

"Sam, I'm going to let that one slide, for now. Let's go inside," Dean said, as he started to make his way inside the families current home. Sam stopped him.

"No. I'm not going to let you in this house to upset her anymore than yo ualready have," Sam stated.

Dean pursed his lips and sighed.

" I'm not going to start anything. I'm going to go to bed. We'll all talk about this in the morning," he said, even though the last past sounded more like a promise.

Sam took one more look in Dean's eyes to make sure he was sincere, before he allowed Dean to enter.

Dean opened the door, and like promised, he made his way to his own room, shutting the door behind him. 


End file.
